1. The timing of life history events, such as germination and reproduction, influences ecological and selective environments throughout the life cycle. Many organisms evolve responses to seasonal environmental cues to synchronize these key events with favorable conditions. Often the fitness consequences of each life history transition depend on previous and subsequent events in the life cycle. If so, shifts in environmental cues can create cascading effects throughout the life cycle, which can influence fitness, selection on life history traits, and population viability. 2. We examined variation in cue responses for contingent life history expression and fitness in a California native wildflower, Streptanthus tortuosus, by manipulating seasonal germination timing in a common garden experiment. We also manipulated chilling exposure to test the role of vernalization cues for seasonal life history contingency. 3. Plants germinating early in the growing season in autumn were more likely to flower in the first year and less likely to perennate than later germinants in spring. First year reproduction and overall fitness was highest for autumn cohorts. Sensitivity analyses showed that optimal germination date depended on survival beyond the first year and fruit production in later years. 4. Experimental chilling exposure induced first year flowering in spring germinants, demonstrating that seasonal life history contingency is mediated by a vernalization requirement. This requirement reduced fitness of spring germinants without increasing survival or later fecundity and may be maladaptive. Such mismatches between cues and fitness may become more pervasive as predicted climate change reduces exposure to chilling, shortens growing seasons, and increases severity of summer drought. 5. Synthesis: Shifts in germination timing in seasonal environments can cause cascading effects on trait expression and fitness that extend beyond the first year of the life cycle. Climate change is likely to shift seasonal conditions, influencing such life history contingency, with significant impacts on trait expression, fitness, and population persistence. These shifts may cause strong natural selection on cue sensitivity and life history expression, but it is an open question whether populations have the potential for rapid adaptation in response to this selection.